Waitt was taught by John Scougall, and began his career as decorative painter of still lifes before moving towards portraiture.
It was unfortunate for Waitt that the 1707 Act of Union saw political power shift to London and with it go Scotland’s patronage. Unlike fellow artists such as William Aikman and John Smibert a move to London may not have been an option. In 1713, Waitt was commissioned by Brigadier Alexander Grant of Grant to paint a series of portraits.
For many years he was to work almost exclusively for the Clan Grant. King William III conferred the status of Regality upon the Grant lands. This gave the Grant of Grant all royal powers, bar that of trial for treason. It only lasted until 1746 but for the duration of Waitt’s painting career this was a place of some import. James Holloway noted that, ‘No other family in Scotland, or in Europe for that matter, commissioned a similar group of portraits of their clan – family, retainers and kinsmen – and it is as a group, rather than as individual paintings, that Waitt’s portraits of Clan Grant should be judged.’